Assassin’s Creed IV Black Flag Resynced has 9 Painting Locations. All of them are needed to fill the Art Collection slots in Great Inagua Manor for the Dilettante trophy & achievement. You can view them under Codex > Database > Art Collection: Paintings.
Paintings are not to be confused with the 
11 Portraits, which are a different type of collectible for another trophy 
The Memory of My Enemy.
The 9 Paintings come exclusively from raiding the 
9 Warehouses. Each Warehouse gives one Painting. They will briefly pop up on the right side after looting the Warehouse, and at the bottom of the Codex menu as your most recently collected item. Getting all Paintings is hence very straightforward: simply loot each Warehouse once. You can filter for Warehouse by pressing D-Pad Down 
on the map. You can still grab them after the story in free-roam. If you’ve already looted Warehouses check the Codex menu which Paintings you are missing. Each Warehouse requires a key that you find in the plantation around the Warehouse. The keys have predetermined locations on the first raid but then become randomized when you loot the Warehouses again.
For 
Dilettante to decorate the manor, you need all 41 Art Pieces (which include table decorations, cabinet decorations, furniture), 9 Paintings, 20 Ship Models, 11 Portraits. They are listed here in Codex order.
Collectibles Overview:
Paintings (Codex Order)
Painting #1: Map of the World
Reward from Tortuga Warehouse.
Key Location (1st Raid): Loot the key from a banana crate, slightly west from the center of the plantation.
Painting #2: Vanitas Still-life
Reward from Kingston North Warehouse.
Key Location (1st Raid): Loot the key from enemy who patrols the manor in the north-east corner of the warehouse area.
Painting #3: An English Ship in Action with Barbary Vessels
Reward from New Bone Warehouse.
Key Location (1st Raid): Loot from enemy at the Mayan Stelae in the north-west corner of the island. He will stand there talking to his girlfriend.
Painting #4: Harbor Scene at Sunset
Reward from Nassau Warehouse.
Key Location (1st Raid): Loot key from enemy at the beach in the south-west of the warehouse area. You can also eavesdrop on two guards at the warehouse who give the hint he has the key.
Painting #5: Merry Company
Reward from Matanzas Warehouse.
Key Location (1st Raid): In the south-west corner of the plantation where a crocodile icon is, loot it from the body behind the crocodile pond on the little corner island.
Painting #6: Nymphs By A Fountain
Reward from Kingston South Warehouse.
Key Location (1st Raid): Loot the key from an enemy directly north of the big barn.
Painting #7: Saint Jerome as Cardinal
Reward from Havana Warehouse.
Key Location (1st Raid): Loot the key from an enemy in the north-west corner of the plantation.
Painting #8: The Burning of the Royal James
Reward from Cat Island Warehouse – automatically looted during Sequence 03 – Mission 05: Sugarcane and Its Yields. You’ll get the Painting automatically during this story quest, no need to loot the Warehouse again.
Key Location (1st Raid): Story-related in Sequence 03 – Mission 05: Sugarcane and Its Yields. Afterward the key will be randomized but you should already have the painting so no need to do it again.
Painting #9: The Flight into Egypt
Reward from Black Island Warehouse.
Key Location (1st Raid): Near the warehouse you can overhear two NPCs talking about the soldier with the key near the beach, then the objective marker updates. He stands at a campfire on the path leading to the south-west beach.
That’s all of the Character Paintings in AC IV Black Flag (2026 Remake). For all other collectible types refer to the Assassin’s Creed IV: Black Flag Resynced Collectible Guide.
KeenEye says
Can’t seem to trigger the one for #9. Any ideas?
Last one I need, too.
PowerPyx says
That one seems to bug out sometimes. If you’ve defeated everyone and never got the key, best hope is to wait for the enemies to respawn (takes 2 hours I think).